Primaquine Diphosphate

Catalog No.S4237 Batch:S423703

Technical Data

Formula	C₁₅H₂₁N₃O.2H₃O₄P
Molecular Weight	455.34	CAS No.	63-45-6
Solubility (25°C)*	In vitro	DMSO	91 mg/mL (199.85 mM)
		Water	91 mg/mL (199.85 mM)
		Ethanol	Insoluble
* <1 mg/ml means slightly soluble or insoluble. * Please note that Selleck tests the solubility of all compounds in-house, and the actual solubility may differ slightly from published values. This is normal and is due to slight batch-to-batch variations. * Room temperature shipping (Stability testing shows this product can be shipped without any cooling measures.)

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Biological Activity

Description	Primaquine Diphosphate is a transmission-blocking anti-malarial clinically available, displaying a marked activity against gametocytes of all species of human malaria.
In vitro	Primaquine is still the only transmission-blocking anti-malarial clinically available, displaying a marked activity against gametocytes of all species of human malaria, including multi-resistant Plasmodium falciparum strains. Primaquine is also effective against all exoerythrocytic forms of the parasite and is used in conjunction with other anti-malarials for the treatment of vivax and ovale malaria. The exact mechanism by which Primaquine so effectively eliminates Plasmodium falciparum and gametocytes is still unknown, but it is thought that metabolism at the parasites’ mitochondria is impaired, eventually by interference with the ubiquinone function as an electron carrier in the respiratory chain. Another potential mechanism of anti-malarial action by Primaquine is the production of highly reactive metabolites that generate intracellular oxidative potentials. Primaquine is found to be an inhibitor of vesicular transport and blocks the calcium-release-activated current in rat megakaryocytes. Primaquine also acts on cardiac Na⁺ channels in isolated rat ventricular muscle and myocytes. Primaquine inhibits protein transport with IC50 of 50 μM, and inhibits the budding of vesicles from the donor membranes. PQ has a strong inhibitory effect on the recycling of endocytosed proteins to the plasma membrane. Primaquine is able to inhibit the potassium current by blockade of muscarinic receptors. Primaquine also inhibit human erythrocyte membrane acetylcholinesterase (AChE) with IC33 of 30 μM. Primaquine is a nitrite-reacting mutagen precursor where the secondary amino group plays a key role. ^[1]

Description

Primaquine Diphosphate is a transmission-blocking anti-malarial clinically available, displaying a marked activity against gametocytes of all species of human malaria.

In vitro

Primaquine is still the only transmission-blocking anti-malarial clinically available, displaying a marked activity against gametocytes of all species of human malaria, including multi-resistant Plasmodium falciparum strains. Primaquine is also effective against all exoerythrocytic forms of the parasite and is used in conjunction with other anti-malarials for the treatment of vivax and ovale malaria. The exact mechanism by which Primaquine so effectively eliminates Plasmodium falciparum and gametocytes is still unknown, but it is thought that metabolism at the parasites’ mitochondria is impaired, eventually by interference with the ubiquinone function as an electron carrier in the respiratory chain. Another potential mechanism of anti-malarial action by Primaquine is the production of highly reactive metabolites that generate intracellular oxidative potentials. Primaquine is found to be an inhibitor of vesicular transport and blocks the calcium-release-activated current in rat megakaryocytes. Primaquine also acts on cardiac Na⁺ channels in isolated rat ventricular muscle and myocytes. Primaquine inhibits protein transport with IC50 of 50 μM, and inhibits the budding of vesicles from the donor membranes. PQ has a strong inhibitory effect on the recycling of endocytosed proteins to the plasma membrane. Primaquine is able to inhibit the potassium current by blockade of muscarinic receptors. Primaquine also inhibit human erythrocyte membrane acetylcholinesterase (AChE) with IC33 of 30 μM. Primaquine is a nitrite-reacting mutagen precursor where the secondary amino group plays a key role. ^[1]

Protocol (from reference)

References

[1] Vale N, et al. Eur J Med Chem, 2009, 44(3), 937-953.

Selleck's Primaquine Diphosphate has been cited by 3 publications

RAB22A sorts epithelial growth factor receptor (EGFR) from early endosomes to recycling endosomes for microvesicles release [ J Extracell Vesicles, 2024, 13(7):e12494]	PubMed: 39051763
Primaquine Diphosphate, a Known Antimalarial Drug, Blocks Vascular Leakage Acting Through Junction Stabilization [ Front Pharmacol, 2021, 12:695009]	PubMed: 34149436
Quantifying Drug Combination Synergy along Potency and Efficacy Axes. [ Cell Syst, 2019, 8(2):97-108]	PubMed: 30797775

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SHIPPING AND STORAGE
Selleck products are transported at room temperature. If you receive the product at room temperature, please rest assured, the Selleck Quality Inspection Department has conducted experiments to verify that the normal temperature placement of one month will not affect the biological activity of powder products. After collecting, please store the product according to the requirements described in the datasheet. Most Selleck products are stable under the recommended conditions.

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